1. Field of the Invention
The invention herein pertains to the field of herbicides. More particularly, the field of this invention pertains to the use of 2-haloacetamides as herbicides.
2. Description of the Prior Art
It is known in the prior art to use various 2-haloacetamides as herbicides, either individually or in combination with other herbicides.
Among herbicidal compounds of the prior art are those acetamides having in varying arrangements substitutions of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkoxy, halogen, aryl, etc. groups, all of which may be further substituted with other radicals.
Illustrative of the 2-haloacetamides of the prior art and of those most closely related to the 2-haloacetamides disclosed and claimed herein are the 2-haloacetamides disclosed in U.S. Pat. Nos. 3,495,967, 3,574,746, 3,586,496, 3,901,917, 3,819,661, 3,946,045, 4,012,222, 4,097,262, 4,055,410 and 4,155,744. In the '967 patent the 2-chloroacetamides are characterized by substitutions on the nitrogen atom including a benzothiophene radical which may have other substituents. The '746 and '496 patents are directed generally to the same 2-haloacetamides which are characterized by a C.sub.5-7 cycloalken-1-yl group and other substituents on the amide nitrogen. The '917 patent relates to 2-haloacetanilides characterized in having a thienylmethylene group which may be substituted with a lower alkyl group substituted on the nitrogen atom and the '661 patent relates to 2-haloacetanilides which are substituted on the nitrogen atom with a furfuryl or tetrahydrofurfuryl. The '045 and '222 patents disclose 2-haloacetanilides characterized by a dioxolanyl-lower alkyl group on the anilide nitrogen atom. The '410 patent relates to 2-haloacetanilides substituted on the nitrogen atom with 2,4-dioxothiazolidinylmethyl or 2,4-dioxoimidazolidinylmethyl radicals and the '744 patent relates to 2-haloacetamides characterized by substitutions on the nitrogen atom of cycloalkenyl and heterocyclic radicals. The '262 patent relates to N-(O-substituted-phenyl)-N-[(2-oxooxazolidin-3-yl)-methyl)-2-haloacetamide s.
Prior art processes for producing various 2-haloacetamides involve the haloacetylation of the appropriate aniline or cyclohexylideneimine to get the corresponding product.
As will be apparent, the most relevant 2-haloacetamides of the prior art have a heterocyclic and cycloalkenyl or phenyl (which may be substituted) group attached to acetamide or acetanilide nitrogen atom. However, this above prior art fails to disclose the novel 2-haloacetamides and process of the present invention as will be apparent from the discussion below.